PHOTOCHEMISTRY OF 2‐MERCAPTOPYRIDINES. PART 3. EPR STUDY OF PHOTOPRODUCTION OF HYDROXYL RADICALS BY N‐HYDROXYPYRIDINE‐2‐THIONE USING 5,5‐DIMETHYL‐1‐PYRROLINE N‐OXIDE IN AQUEOUS SOLUTIONS*

作者: Krzysztof J. Reszka , Colin F. Chignell

DOI: 10.1111/J.1751-1097.1995.TB03970.X

关键词: Adduct5 5 dimethyl 1 pyrroline n oxideAqueous solutionFormateAlcoholElectron paramagnetic resonanceChemistryIrradiationRadicalPhotochemistry

摘要: —N-Hydroxypyridine-2-thione, 2-S-PyrNOH, a potent antimicrobial, antifungal and anticancer agent, is photochemically active upon UV irradiation generates free radicals. We have employed EPR the spin-trap 5,5-dimethyl-l-pyrroline TV-oxide (DMPO) to investigate photochemistry in aqueous solutions of 2-S-PyrNOH (used here form sodium salt, 2-S-PyrNONa). found that photoactivation 2-S-PyrNONa can follow two different pathways: it produce hydroxyl radicals and/or act as photoreducing agent. The capacity “OH” has been demonstrated by: (1) detection DMPO/OH adduct UV-irradiated samples; (2) inhibition formation by OH scavengers such methyl alcohol, formate DMSO (3) signals DMPO adducts with derived from reaction these inhibitors. photoreductive was deduced observation amplitude signal spin decreased on air-free pH 7.0 buffers recovered dark after aeration. ability generate suggests be regarded potential photocytotoxic This feature may relevant biological action this compound. Our findings also emphasize caution should used when source or chemical systems.

参考文章(15)
George J. Kontoghiorghes, Andrea Piga, A. Victor Hoffbrand, Cytotoxic and DNA-inhibitory effects of iron chelators on human leukaemic cell lines Hematological Oncology. ,vol. 4, pp. 195- 204 ,(1986) , 10.1002/HON.2900040303
Derek H.R. Barton, Joseph Cs. Jaszberenyi, Andrew I. Morrell, The generation and reactivity of oxygen centered radicals from the photolysis of derivatives of N-hydroxy-2-thiopyridone. Tetrahedron Letters. ,vol. 32, pp. 311- 314 ,(1991) , 10.1016/S0040-4039(00)92615-7
Angelo Albini, Marco Alpegiani, The photochemistry of the N-oxide function Chemical Reviews. ,vol. 15, pp. 43- 71 ,(1984) , 10.1021/CR00059A004
Phillip M. Hanna, Walee Chamulitrat, Ronald P. Mason, When are metal ion-dependent hydroxyl and alkoxyl radical adducts of 5,5-dimethyl-1-pyrroline N-oxide artifacts? Archives of Biochemistry and Biophysics. ,vol. 296, pp. 640- 644 ,(1992) , 10.1016/0003-9861(92)90620-C
R. Alan Jones, A. R. Katritzky, 593. N-oxides and related compounds. Part XVII. The tautomerism of mercapto- and acylamino-pyridine 1-oxides Journal of The Chemical Society (resumed). pp. 2937- 2942 ,(1960) , 10.1039/JR9600002937
D.R. Duling, Simulation of Multiple Isotropic Spin-Trap EPR Spectra Journal of Magnetic Resonance, Series B. ,vol. 104, pp. 105- 110 ,(1994) , 10.1006/JMRB.1994.1062